Burgess reagent

Burgess reagent
Names
IUPAC name
1-Methoxy-N-triethylammoniosulfonyl-methanimidate
Identifiers
CAS Number
  • 29684-56-8 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 2007108
ECHA InfoCard 100.157.812 Edit this at Wikidata
EC Number
  • 629-648-8
PubChem CID
  • 2724994
UNII
  • H5HBH02LFX checkY
CompTox Dashboard (EPA)
  • DTXSID90894112 Edit this at Wikidata
InChI
  • InChI=1/C8H18N2O4S/c1-5-10(6-2,7-3)15(12,13)9-8(11)14-4/h5-7H2,1-4H3
    Key: YSHOWEKUVWPFNR-UHFFFAOYAN
  • O=S(=O)(N=C([O-])OC)[N+](CC)(CC)CC
Properties
Chemical formula
 C8H18N2O4S
Molar mass 238.30 g·mol−1
Hazards
GHS labelling:
Pictograms
 GHS07: Exclamation mark
Warning
Hazard statements
 H315, H319, H335
Precautionary statements
 P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound

The Burgess reagent (methyl N-(triethylammoniumsulfonyl)carbamate) is a mild and selective dehydrating reagent often used in organic chemistry.[1][2] It was developed in the laboratory of Edward M. Burgess at Georgia Tech.

The Burgess reagent is used to convert secondary and tertiary alcohols with an adjacent proton into alkenes. Dehydration of primary alcohols does not work well. The reagent is soluble in common organic solvents and alcohol dehydration takes place with syn elimination through an intramolecular elimination reaction. The Burgess reagent is a carbamate and an inner salt. A general mechanism is shown below.

General Mechanism for the Burgess reagent.

Preparation

The reagent is prepared from chlorosulfonylisocyanate by reaction with methanol and triethylamine in benzene:[3]

Burgess reagent

References

  1. ^ Atkins, G. M.; Burgess, E. M. (1968). "The reactions of an N-sulfonylamine inner salt". J. Am. Chem. Soc. 90 (17): 4744–4745. doi:10.1021/ja01019a052.
  2. ^ Sachin Khapli, Satyajit Dey & Dipakranjan Mal (2001). "Burgess reagent in organic synthesis" (PDF). J. Indian Inst. Sci. 81: 461–476. Archived from the original (PDF) on 2004-03-02.
  3. ^ Edward M. Burgess; Harold R. Penton Jr. & E. A. Taylor (1973). "Thermal reactions of alkyl N-carbomethoxysulfamate esters". J. Org. Chem. 38 (1): 26–31. doi:10.1021/jo00941a006.